


Connect

by bauldlad



Category: Critical Role (Web Series)
Genre: 100 percent tender, 40 percent hair braiding, 60 percent smooching, F/M
Language: English
Status: Completed
Published: 2020-09-22
Updated: 2020-09-22
Packaged: 2021-03-07 16:14:52
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,760
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26600479
Author URL: https://archiveofourown.org/users/bauldlad/pseuds/bauldlad
Summary: Jester gives Caleb's hair the attention it deserves.
Relationships: Jester Lavorre/Caleb Widogast
Comments: 19
Kudos: 162





	Connect

"Cay-leb! Are you busy?"

Jester creaks the door to the study open and pokes her head through, letting her eyes wander around the room. It isn’t too big, far smaller than the library of Caleb’s mansion but still staked with books all the way up the impossibly high ceilings. Her eyes fall to Caleb’s desk, where his familiar form sits hunched over a massive pile of parchment.

Caleb straightens up, only barely turning his head to regard her. "Yes, but it's nothing I can't put down.”

“Well, I’m bored,” she announces, making her way to Caleb’s back to peer over his shoulder. This was only partly true, she could find a way to entertain herself alone, she’d done it all her life. She just didn’t want to. 

Caleb’s notes are surprisingly neat (his handwriting isn’t the cutest) even if she didn’t understand a word of them. She scrunches her nose at this and walks instead to Frumpkin, who lounges idly atop an empty shelf, and takes the cat into her arms.

She buries her face into his fur and watches Caleb, who spares her a brief glance before turning his attention back to his notes.

“I’m not sure there’s much I can do about your boredom,” he says, carefully dipping his pen into ink. “I’m quite boring myself, if you haven’t noticed that about me by now.”

Jester sighs loudly and puts Frumpkin back down, making her way to Caleb’s side again. “Can I hang out with you? We can talk for a while or something.”

Caleb looks up at her, and Jester can see him exhale deeply. She frowns, thinking maybe she’s bothered him. But no, he gives her a small smile and that concern is gone quickly, though it always lingers.

“I’m not sure I’ll make the most fascinating conversation at this moment, but- “

“Ooh!” She claps once, interrupting him. “What if I braided your hair? It’s been _forever_ and look at how long and pretty your hair looks now!”

Caleb looks incredulously at her, idly pushing his bags behind his ear. Jester smiles at how bashful he looks, leaning closer towards him.

“Don’t think I forget how much you liked it last time,” she says lightly, smile widening at how his cheeks turn a light pink.

Caleb clears his throat and shrugs, rubbing the back of his neck. “Ah, sure. I suppose I wouldn’t mind.”

Jester’s grin is almost wicked now. “Great! It’s a good thing I’m carrying this comb with me, eh?”

Caleb rolls his eyes, but she can see a smile on his face as she moves to his back. She picks up his ponytail and inspects the ends, tutting at how split the ends are and making a mental note to offer a real haircut next time.

“Don’t you worry, Caleb, just keep doing what you’re doing, and I’ll handle this.”

There’s a pause before she hears Caleb’s pen moving again. “All right then, Jester. No strange dick braids or anything, ja?”

Jester cackles as she loosens Caleb’s ponytail, startling at how his red hair is longer and more voluminous up close. She lets out a small ‘ooh’ and leans her head near his, comparing the length of her own hair.

“Wow, Caleb! Keep this up and your hair will be even longer than mine!” She stands straight again and starts running her comb down the length of his hair. “I bet we’d look super cute with matching hairstyles!”

“I think I’ll leave the buns to you,” he replies, monotone as always but Jester can sense the smile on his face.

She configures Caleb’s hair into a few loose styles, seeing what she could manage with his length. Finally, she settles on a half braid, one on either side of his head, and gets to work.

The scratching of Caleb’s pen along parchment is all that can be heard between them as Jester continues lacing through his hair with her comb, working out the knots. Jester enjoys the silence, strangely. She finds it’s easy to do so when it’s Caleb especially.

But there was a reason she wanted to see him, hair braiding aside. She bites her bottom lip in thought for a while, not wanting to break the silence. Finally, she sighs and closes her eyes, bracing herself to be chased away.

"You didn't answer me before."

"Pardon?" Caleb doesn’t stop writing, and Jester lets out a sigh of relief. She’s not sure why she thought he’d be upset. He never has been before. Emboldened, she continues, louder this time.

"After the dinner, when I asked if you were okay." She stops combing for a moment to fidget with the ends of his hair. "You never answered."

After a pause, he sighs, shaking his head. Jester gently holds his head in place, and he gives her a murmured apology.

"Honestly? I'm not okay, no. But I think... I- I don't know." He sighs again, and Jester just wants to wrap her arms around him and say _yes, Caleb. Yes. I know. I'm not okay either and that's okay._

But instead she puts her comb down and runs her fingers through his hair. Less to get it neat and more for comfort. "Things won't be okay overnight, but... It will be one day."

Silence, for a while. "Maybe so, Jester."

She gently combs through his hair a few more times, enjoying the feel against her fingers. She can see the pace of his writing slow as she brushes the tips of her fingers along the crown of his head.

“Does that feel okay?” she asks in a soft tone. Not too loud, not to scare him away.

Caleb’s nod is immediate, and Jester smiles, her heart beating considerably faster as she lets her fingers fall along his head for a while longer. After a second, she sections out the hair on his left and starts twisting a neat braid. They’re quiet again as she finishes the first side, though Jester softly hums a tune to herself, fingers moving in time with the slow melody.

As she pats down the first braid, she peeks her head around to see Caleb’s face. She’s almost overcome with affection when he meets her eyes and smiles softly, gently touching the braid with his free hand.

“How does it look?”

Perfect? Stunning? Maybe the most beautiful thing she’s ever seen, and she’s seen _a lot_ of beautiful things. She opens her mouth to reply and… nothing. Traveler save her. She just gives him a thumbs up and moves back behind him, eyes wide.

Jester palms restlessly at his still loose hair before she exhales deeply and lets her head fall onto Caleb’s. Her chin rests on the top of his head, her eyes closing before she can see Caleb’s reaction. She settles a hand on Caleb’s shoulder and nearly jumps out of her skin when Caleb’s hand falls on top of hers.

“Ah, Jester? Are you all right?”

His voice is so concerned, and it sends a flow of warmth down her body. “I don’t know… Right now, specifically? I’m really good but in general? Not really. So… I don’t know.”

Caleb’s hand tightens around hers. “I suppose we’ll have to stay confused together, then.”

Jester laughs at this, weak and breathy, and she lets her cheek nuzzle across Caleb’s head. Caleb unclasps his hands from hers and she hears him return to writing. She bites her lip and looks up at the ceiling, working up the courage to speak again.

"Hey Caleb? Would you mind if I kissed you?"

The scratching of parchment stops. "If you... If you... What?"

Her blush deepens and now she feels stupid, how could she suggest something so silly? Now he'll think she's, what? Desperate and hopeless all over again, like with Fjord, and... She isn't that. Or at least, she shouldn’t be like that. She scrambles to keep talking, voice a little too loud.

"Just like, on your _hair_! Mama would do it all the time when she did my hair and it always made me feel..." She trails off, mentally hitting herself. Well now she sounds like she wants to be Caleb's _mom_ or something! She covers her face and shakes her head, letting out a groan.

"It helps me feel better, okay?" Jester finishes lamely, voice tiny now. She almost thinks Caleb didn't hear her, he's quiet for so long. Finally, just when she decides to just bolt out of the room and spend the night in a separate plane of existence—

"Ja, sure. Sure, you can."

If she weren't on the verge of sinking to the ground, she would have giggled at how nervous he sounded, his voice high and clipped. She can only smile weakly and pat Caleb’s head, biting the inside of her cheek to keep from saying anything else and ruining things.

She kisses the braid she just finished before moving to the back of his head, keeping her nose buried in his red hair. She plants a few kisses to the back of his head, tightening her hold on Caleb's shoulders to still her shaking hands. She can't remember a time she's ever been this nervous.

She can see the tips of his ears have gone entirely red, and his shoulders tense up. She loosens her grip on them and rubs gently, working in small circles. Her lips stay fixed to the back of his head, afraid to move, to scare Caleb away and end the moment with her overenthusiasm. She kneads silently at his shoulders until they finally lower and takes the opportunity to move her head to where his shoulder meets his neck. 

"Jester..." Caleb's voice is low, his accent thick. "Are you sure?"

Jester shuts her eyes, still leaning her forehead against the crook of his neck. "That depends... Did you like it?"

"I..." He quiets, letting a shaky breath. "Jester. I did. I do."

She doesn't need to hear any more. She presses a kiss to his neck, and moves slowly up his jaw and to his ears, still red. She savors the way his irregular breaths even out as she continues, imagining it against her own face.

"Caleb..."

Caleb's voice is just a whisper now. "What is it?"

She presses a kiss to the back of his jaw again, before running her palm along the underside of his long hair, rubbing the back of his neck. She lifts his hair into a makeshift bun in her hands and leans down to press a kiss to the back of his neck, letting the hair fall from her hands and down her face as she places a few more kisses in the same spot.

"Ah… Jester?"

She's still for a few moments before murmuring, "It's nothing. I just wanted to say your name."

He turns and she can see his face properly, and oh, it is almost too much. His eyes half lidded looking up at her, face colored a beautiful red that runs down to his neck. His chest is rising and falling rapidly, and she wants to reach out and press her head to it, see if his heart is racing as much as hers and press against him to show him how painfully hers beats.

Jester uses the arms of Caleb's chair to physically turn it towards her and lean herself closer to Caleb though they prevent her from doing much more than that. She pulls uselessly at the arms and Caleb doesn't even spare them a glance, keeping his eyes on her as his hand raises and the arms of the chair disappear.

Losing her leverage, Jester lets out a small yelp and falls forward only to be stopped by Caleb's arms around her waist. Caleb stares directly at her, gaze insistent and just a bit wild but so painfully fond she can't believe she's been missing out on this for so long.

She doesn't hesitate a second longer as she climbs onto his lap, immediately taking his head into her hands. She's peppering kisses all over his jaw and cheeks. She holds her breath as she does so, not wanting to miss a single sound coming from Caleb. She smiles at his surprised hum as she presses a kiss to the dimple on his chin. She positively grins at his gasp as her attention moves down to his Adam's apple, nuzzling his neck affectionately with her nose. She shudders at the soft moan she draws out when she trails kisses along his chest, near his collar where his shirt is unbuttoned.

Jester places a few more kisses there before Caleb's hands are on her head and running through her hair gently. She feels exposed and slightly awkward as he tilts her head back up towards his.

Their eyes meet and she flushes at his searching gaze, noticing the faint worry playing at his brow. She smiles shyly and nods as if to confirm that _yes, Caleb, this is all okay._

The worry leaves his face and his lips part, then Jester barely has time to react to the chaste kiss Caleb gives her. It's so brief but so _warm_ her eyes start to water. She definitely wouldn’t have expected to _cry_ after her first kiss (and this is officially her REAL first kiss!) but she can’t help the swell of relief that hits her.

Caleb's face is so close as he pulls away Jester can see his faint freckles tinted red along with his lips, bitten up by Caleb's worrying. She brushes her lips across his cheek, sighing at the warmth under her mouth.

"Caleb, again…" His breath tickles at her lashes and she closes her eyes, waiting.

"Oh, Jester." His lips catch hers once again and this time it's so much slower and searching. Caleb's arms tighten around Jester's waist and he draws her closer and tilts his head and _oh,_ she's way in over her head with this wizard because he is so much more talented than she imagined she could ever be. 

They pull away for just a moment to breathe, not really looking at each other, before Jester pulls him back in by his shirt. She runs her hands along his shoulders, roaming along his sides until they finally fall on Caleb's hair again and tangle into his long waves, pulling his head closer because she wants _more,_ she can't get close enough. Jester pushes their heads so close they can barely move their lips, drawing a chuckle from Caleb as he pulls away to peck the side of her mouth and look up at her properly.

He runs his hands across his hair, what little Jester had done already mussed up and ruined by her own grip. She smiles apologetically, pulling her hands away from his head and leaning back.

“I kind of messed that up, didn’t I?” She lets her hands fall on her legs instead, still straddling him. She doesn’t feel the least bit sorry.

A small smile plays on his face as he feels the braid she'd finished. "I suppose the half-finished look is very interesting."

Jester laughs, and playfully bats her hand across his shoulder. "I don't know Cay-leb, you look very beautiful to me.” She wiggles her eyebrows at him as her hands move to his cheeks. "It sort of looks like you finished boning. If you want to look that way..."

She immediately feels his face heat up under her hands and his eyes widen slightly, the flustered look familiar and comforting to Jester in a strange way. Like things haven’t changed, or at least not in a bad way. She giggles as he gently takes her arms and moves them down, taking her hands in his own.

He leans his head on her shoulder, speaking muffled into her neck.

"That's a look for another day, I think," he says and it's her turn to blush, though she can't help a laugh as she turns her head to kiss his.

After a moment, Jester stands and gently pulls free a lock of Caleb's hair, twisting it around her fingers. "Then let me finish up?"

He looks away in exaggerated thought before finally shrugging. "If you insist..."

"Ooh! I can braid a ribbon into your hair! Can I braid a ribbon into your hair?"

She absolutely melts at the laugh Caleb lets out as he turns his chair back to face his desk. "For you, Blueberry? Anything."

A laugh of her own this time, and she tugs playfully at his hair. "Oh, you'll regret saying that, Caleb…"

**Author's Note:**

> I'll continue my habit of putting no thought into a title until I die.
> 
> I wrote the bulk of this half asleep desperate to get the idea out so I mean... I hope it's okay.


End file.
